methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[4-[(2-methylpropan-2-yl)oxy]phenyl]butanoate | 507276-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[4-[(2-methylpropan-2-yl)oxy]phenyl]butanoate
• CAS: 507276-78-0
• 化学式: C₂₀H₃₁NO₅
• 分子量: 365.47
• InChiKey: NMMRESZNBOESTJ-HNNXBMFYSA-N

物化性质

• 沸点：
  477.0±45.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[4-[(2-methylpropan-2-yl)oxy]phenyl]butanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) lithium hydroxide 、 双氧水 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 5.5h， 生成 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enoic acid
  参考文献：
  名称：

  Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols

  摘要：

  [GRAPHICS]Using olefin cross-metathesis, we synthesized a novel stereodiversified library of compounds 3 containing a trans-1,4-enediol. Screening this library for mu opioid receptor (MOR) affinity identified multiple high-affinity ligands and revealed that the stereochemical configuration varied widely among those ligands having the highest affinity. It was not possible to predict the configurations of the most active compounds 3 on the basis of the configuration of endomorphin-2, a known MOR peptide ligand, validating the diversity-based approach to ligand discovery.

  DOI：

  10.1021/ol027237f
• 作为产物：
  描述：

  Boc-O-叔丁基-L-酪氨酸 在 N-甲基吗啉 、 silver benzoate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[4-[(2-methylpropan-2-yl)oxy]phenyl]butanoate
  参考文献：
  名称：

  Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols

  摘要：

  [GRAPHICS]Using olefin cross-metathesis, we synthesized a novel stereodiversified library of compounds 3 containing a trans-1,4-enediol. Screening this library for mu opioid receptor (MOR) affinity identified multiple high-affinity ligands and revealed that the stereochemical configuration varied widely among those ligands having the highest affinity. It was not possible to predict the configurations of the most active compounds 3 on the basis of the configuration of endomorphin-2, a known MOR peptide ligand, validating the diversity-based approach to ligand discovery.

  DOI：

  10.1021/ol027237f

文献信息

• Kinetic deconjugation: a gateway to the synthesis of Xxx-Gly (E)-alkene dipeptide isosteres
  作者：Arnaud Proteau-Gagné、Jean-François Nadon、Sylvain Bernard、Brigitte Guérin、Louis Gendron、Yves L. Dory

  DOI：10.1016/j.tetlet.2011.09.136

  日期：2011.12

  A new method for the preparation of Xxx-Gly (E)-alkene dipeptide isosteres (EADIs), using LDA deprotonation followed by 1 N HCl quench, was explored. The method, named kinetic deconjugation, enabled the synthesis of Tyr-Gly, Gly-Gly, Ser-Gly, Pro-Gly, and Phe-Gly EADIs, as well as one Tyr-Gly trisubstituted alkene dipeptide isostere (TADI). Overall, this method, based on commercially available materials

  探索了一种新的制备Xxx-Gly（E）-烯烃二肽等排物（EADIs）的方法，该方法使用LDA脱质子化，然后用1 N HCl淬灭。该方法称为动力学解偶联，能够合成Tyr-Gly，Gly-Gly，Ser-Gly，Pro-Gly和Phe-Gly EADIs，以及一种Tyr-Gly三取代烯烃二肽等排物（TADI）。总体而言，该方法基于可商购的材料，可实现高收率，仅需很少的合成步骤，并且可以在多种EADI的合成中达到克级。
• Mu opioid receptor ligands: methods of use and synthesis
  申请人：Harrison Bryce A.

  公开号：US20090093534A1

  公开（公告）日：2009-04-09

  Novel compounds and compositions including those compounds, as well as methods of using and making the compounds are herein described. The compounds are useful in therapeutic applications, including modulation of disease or disease symptoms in a subject (e.g., mammal, human, dog, cat, horse). The compounds are useful as modulators of the mu opioid receptor (MOR) through their binding affinity with that receptor.

  本文描述了包括这些化合物在内的新型化合物和组合物，以及使用和制造这些化合物的方法。这些化合物在治疗应用中有用，包括调节受试者（例如哺乳动物、人类、狗、猫、马）的疾病或疾病症状。这些化合物通过它们与μ阿片受体（MOR）的结合亲和力作为MOR的调节剂是有用的。
• US7223888B2
  申请人：——

  公开号：US7223888B2

  公开（公告）日：2007-05-29
• US7759514B2
  申请人：——

  公开号：US7759514B2

  公开（公告）日：2010-07-20